


My Gay Thing

by Sams_Princess



Category: Supernatural
Genre: Dean Winchester's First Time With a Man, First Time, Gay Thing, Implied/Referenced Cheating, M/M, No Smut, Stag Nights & Bachelor Parties, Stripper Castiel, Weddings
Language: English
Status: Completed
Published: 2017-07-15
Updated: 2017-07-15
Packaged: 2018-12-02 15:05:00
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,475
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11511861
Author URL: https://archiveofourown.org/users/Sams_Princess/pseuds/Sams_Princess
Summary: Dean's getting married tomorrow morning.So, when Sam promises him a stipper, he expects a beautiful, busty, young woman. What he doesnt expect is his first gay thing.





	My Gay Thing

**Author's Note:**

> Someone over on Facebook asked me for stripper-cas. I set out with something completely differnt than this, but the story wrote itself. I'm not sure exactly what the prompter wanted, so i hope they enjoy!!

Dean leant against the doorframe watching as his fiancé got herself ready for her night out. She had been pampering herself all afternoon, preparing herself for her hen party.

As she applied her final coat of lipstick she noticed his reflection in her dresser mirror. She didn’t turn to look at him, but smiled brightly as their eyes met.

“I could watch you for hours,” Dean admitted quietly, pushing off of the doorframe and walking towards her. He placed his hands gently on her shoulders and squeezed reassuringly. He was so in love with this woman, and had been since they met back when they were only 20.

“Oh, that’s creepy,” Lisa laughed, throwing her head back to rest against Dean’s chest.

“You look stunning,” Dean whispered, ignoring her comment with a smirk. He lowered his head to press a kiss to her cheek.

“Thank you,” She whispered back, reaching up her own hands to intertwine with his. “I see you’ve made no move to doll yourself up.”

“Babe; when you look this good…” Dean trailed off with a laugh as Lisa stood up with a playful cry.

“The cheek!” She commented, slapping him harmfully on the shoulder. She walked past him towards their bed when a pair of very high, red heels waited for her to slip on her feet.

“Any ideas what the girls have planned?” Dean asked, slipping his hands into his pocket. He couldn’t help but check out her cleavage as she bent down to put her shoes on.

“Not a clue,” She admitted, fully aware what her future husband was doing. “But apparently it’s going to be good.” When she sat back up, shoes strapped securely to her feet she smiled at Dean. “How about you? What’s Sam got planned for you?”

“Something about a club and a stripper,” Dean shrugged casually, eyes following her every movement as she stood to grab her clutch bag and her mobile.

“A stripper? Well, Mr Winchester – I hope you don’t plan on running off with some fake-titted bimbo the night before our wedding,” The talk was playful, but both man and woman knew that there was no chance of that happening.

****

There was music and alcohol in the private room that Sam had hired for the night. The room held about 5 of Dean’s closest male friends, and the mood was great. As best man, and organiser of the stag-do, Sam had made a speech and announced the evening commenced; it was too cheesy in Dean’s opinion, but he’d let Sam get on with it.

After Dean had a few drinks in him and had started to relax a bit more, Sam called in the surprise. And the surprise came in the shape and form of a huge pop-out cake. All the guys, Dean included, started hollering. The stripper had arrived and they were getting excited!

Instead of the usual uproar that usually erupted when the cake popped open, silence fell on the room. Because standing in the cake was not a beautiful, busty, young girl; nope, in her place was a rather attractive man.

“Dude – you ordered a guy stripper?” Dean asked Sam in disbelief.

“Uh,” Sam swallowed. “I asked for a dark-haired beauty.”

“You didn’t think to specify the sex?” Dean gaped.

And suddenly, everyone started laughing.

The stripper, looked around the room, finding the situation quite amusing himself.

“So, which of you men is the lucky man?” He asked, climbing his way out of the cake.

6 fingers pointed in Dean’s direction.

“So, you must be Dean,” The stripper licked his lips as he started towards him. Every step closer the man took, Dean took one back, until the back of his legs hit a chair, halting him in place. “I’m Castiel.”

And Castiel was a very attractive young man. He really was a dark-haired beauty. It was just, Dean didn’t swing that way.

Dean gulped as Castiel stopped just mere centimetres in front of him.

“Have you ever had a gay-thing Dean?”

Dean, couldn’t bring himself to speak, and immediately started shaking his head vigorously.

“Well,” Can spoke gruffly, eyes clouding over. He placed his hands on Dean’s shoulders. “Perhaps I can change that,” And with that, he pushed Dean backwards.

Dean fell into the chair behind him, and gasped in shock when Castiel sat himself in his lap. The men around them started hollering and cheering again and Dean’s cheeks turned bright red. Castiel linked his arms around Dean’s neck and brought himself higher again, to whisper into the groom’s ear.

“I promise you’ll enjoy it.”

“I…” Dean stumbled, not sure what he wanted to say. He knew he should push this stripper off – he wasn’t gay, and he was also pretty sure he didn’t want a ‘gay thing’; yet he couldn’t bring himself to do that. This guy was smoking, and Dean was certain that if there was anyone he was going to go gay for, it would be for someone like Castiel.

“Shh,” Castiel pressed a finger to Dean’s lips. “Don’t speak.” A few kisses were peppered against Dean’s jaw. “Just relax and enjoy. You’re going to have the time of your life.”

Castiel pointed towards one of the men, who understood the cue. A few moments later, there was some up-beat, typical stripper kind of music. And that’s when the party really got started.

***

Dean blinked awake. He recognised the hangover straight away, but knew he was lucky that it was only as mild as it was – after all, he had had quite a bit to drink. He groaned and rubbed his hands down his face as he tried to will the dull ache in his head away.

Sitting up, Dean was made aware of a slight pain in his lower back; and he was instantly reminded of the events that took place the night before.

He quickly checked the bed beside him and let out a sigh of relief when he found it empty. The last thing he needed to do was wake up next to a man he had let fuck him, on the morning of his wedding.

Down in the kitchen, Sam was making a light breakfast for them. He chuckled when he saw the state of his brother.

“Good morning Mr Winchester,” He greeted with a smirk. “I saw your gay-thing out about 30 minutes ago.”

“Fuck off,” Dean grumbled helping himself to the readymade coffee. “And promise me you won’t tell Lisa about this!”

“Don’t you worry about it,” Sam reassured. “I’ve already spoken to the group, and we’ve all agreed to take it to the grave.”

****

Their vows had been read, and the rings exchanged. They were now at the reception venue, the hall alive with buzz and chatter as everyone waited for their starters.

Dean held Lisa’s hand as the two spoke about their new lives together.

Although he loved this woman, he couldn’t stop thinking about Castiel. And Dean had realised that he’d started to take more interest in the males that were around – even slightly more than the females. Even the priest who had wed them had been kinda hot!

Dean was definitely starting to question his sexuality.

Suddenly waiters and waitresses started piling out of a ‘staff-only’ door carrying two plates each.

“Congratulations to the happy couple,” A very familiar voice spoke as plates were placed in front of the bride and groom.

Dean’s head shot up, and sure enough stood in front of him was Castiel.

The stripper (or Dean guessed now, waiter) winked before moving backwards and away from the table.

Later, after the main meal, Lisa excused herself to the toilet. The waiters and waitresses started to come around and clean up the plates. And of course, Dean found himself face to face with Castiel again.

“What are you doing here?” He whispered, trying not to draw attention to himself.

“Waiter by day; stripper by night,” Castiel shrugged. “I enjoyed last night, by the way. And I know you did too,” The waiter picked a clean napkin from his pocket and handed it over to Dean. “You’ve got a little something on your face, Sir.”

Instinctively, Dean used the napkin to wipe the corners of his mouth. But as he pulled the tissue away, he noticed a number written on the back of it.

“If you get bored. Give me a call,” Castiel said with a wink.

“I am not cheating on my wife!” Dean hissed in horror.

“It’s up to you,” Castiel shrugged again and walked off with the plates in his hands.

Dean looked down at the number written neatly on the napkin and thought about discarding it. But then Lisa came back and sat herself back down.

“Who was that?” She asked.

“Just some over friendly waiter,” Dean shrugged, pocketing the napkin in his upper pocket… just in case.

**Author's Note:**

> [My tumblr!!](https://samsprincess69.tumblr.com/)  
>  If you liked my work and would like to buy me a [coffee](https://ko-fi.com/samsprincess), please do!! It would be ever so appriciated!! <3  
> Thank you for all your support!!  
> Much love to you all!  
> xxxx


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